| Identification | Back Directory | [Name]
KADETHRIN | [CAS]
58769-20-3 | [Synonyms]
ru15525
ent29117
spray-tox
KADETHRIN
AI3-29117
Kadethrine
BRN 1605066
cis-kadethrin
1r,cis-ru15525
EINECS 261-433-0
Caswell No. 516AA
KADETHRINE STANDARD
KADETHRIN PESTANAL
5-benzyl-3-furylmethyl
)-cyclopropanecarboxylate
KADETHRIN PESTANAL 250 MG
UGWALRUNBSBTGI-ZKMZRDRYSA-N
yl)cyclopropanecarboxylate.
Kadethrine@100 μg/mL in Methanol
o-3(2h)-thienylidene)methyl]-2,2-dimethylcyclopropanecarboxylate
(5-(phenylmethyl)-3-furanyl)methylester,(1r-(1-alpha,3-alpha(e)))-imethyl
[1r-[1alpha,3alpha(e)]]-[5-(phenylmethyl)-3-furanyl]methyl3-[(dihydro-2-ox
5-benzyl-3-furylmethyl(e)-(1r)-cis-2,2-dimethyl-3-(2-oxothiolan-3-ylidenemeth
cyclopropanecarboxylicacid,3-((dihydro-2-oxo-3(2h)-thienylidene)methyl)-2,2-d
5-benzyl-3-furylmethyl(e)-(1r,3s)-2,2-dimethyl-3-(2-oxothiolan-3-ylidenemethyl
3-((dihydro-2-oxo-3(2h)-thienylidene)methyl)-2,2-dimethyl-,(5-(phenylmethyl)-3-furanyl)
5-benzyl-3-furylmethyl(+)-cis-(1r,3s,e)2,2-dimethyl-3-(2-oxo-2,3,4,5-tetrahydrothiophenylidenemethy
[5-(PHENYLMETHYL)-3-FURANYL]-METHYL-3-[(DIHYDRO-2-OXO-3(2H)-THIENYLIDENE) METHYL]-2,2-DIMETHYLCYCLOPROPANE
3-((dihydro-2-oxo-3(2h)-thienylidene)methyl)-2,2-dimethyl-,(5-(phenylmethyl)-3-furanyl)methylester,cyclopropanecarboxylicaci
[5-benzyl-3-furyl]methyl [1R-[1alpha,3alpha(E)]]-3-[(dihydro-2-oxo-3(2H)-thienylidene)methyl]-2,2-dimethylcyclopropanecarboxylate
(1R,3S)-3-[[(E)-4,5-Dihydro-2-oxothiophen-3(2H)-ylidene]methyl]-2,2-dimethylcyclopropanecarboxylic acid (5-benzyl-3-furyl)methyl ester
(1R,3S)-3-[(E)-(Dihydro-2-oxo-3(2H)-thienylidene)methyl]-2,2-dimethylcyclopropanecarboxylic acid [5-(phenylmethyl)-3-furanyl]methyl ester
Cyclopropanecarboxylic acid, 3-[(E)-(dihydro-2-oxo-3(2H)-thienylidene)methyl]-2,2-dimethyl-, [5-(phenylmethyl)-3-furanyl]methyl ester, (1R,3S)- | [EINECS(EC#)]
261-433-0 | [Molecular Formula]
C23H24O4S | [MDL Number]
MFCD16657115 | [MOL File]
58769-20-3.mol | [Molecular Weight]
396.5 |
| Chemical Properties | Back Directory | [Melting point ]
31℃ | [Boiling point ]
526.2±50.0 °C(Predicted) | [density ]
1.278±0.06 g/cm3(Predicted) | [vapor pressure ]
5×10-6Pa (20 °C) | [Fp ]
100 °C | [storage temp. ]
0-6°C | [Water Solubility ]
1mg l-1（20°C） | [EPA Substance Registry System]
Kadethrin (58769-20-3) |
| Hazard Information | Back Directory | [Uses]
Kadethrin is used to control household pests, particularly houseflies,
mosquitoes and cockroaches. It is normally used in combination
with other pyrethroid insecticides and synergists. | [Metabolic pathway]
Kadethrin is used almost wholly indoors and therefore little has been
published on its environmental fate. Information on its photodegradation
and metabolism in rats has been reported. | [Degradation]
Kadethrin is unstable to heat and it is rapidly decomposed by light. It
is hydrolysed in aqueous alkaline solution to (E)-(1R)-cis-2,2-dimethyl-3-
(2-oxothiolan-3-ylidenemethyl)cyclopropanecarboxylic acid (2), 5-benzyl-
3-furylmethanol (3) and its thiolactone ring-opened derivative (5)
(Scheme 1).
Products of photodecomposition have been reported by Ohsawa and
Casida (1979). Photo-hydrolysis of kadethrin occurs on sunlight irradiation
affording 2 and 5 and 5-benzyl-3-furancarboxylic acid (4), presumably
via the alcohol (3). cis-trans Isomerisation of the cyclopropane ring
and E-Z interconversion about the double bond was also noted. Thus,
from the lRcisE isomer (kadethrin), all of the possible isomers were found
to varying degrees (ie. 1RScis-trans-E-Z mixtures).
Photo-hydrolysis products (e.g. 2 and 5) were also found aS isomers.
The facility of the isomerisation process was considered to be due to
resonance stabilisation of a triplet diradical, one form of which (6) is
shown in Scheme 1. Kadethrin also yielded a lactone (7) derived from the
cyclopropane ring. Photo-oxidation of the alcohol moiety analogous to that reported for resmethrin was also found. The hydroxylactone (8) and
the benzyloxylactone (9) were reported (but the hydroxycyclopetenolone
[resmethrin, 61) was absent. |
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